Pyridyl amines have been used to prepare Group 4 complexes which are useful transition metal components for the polymerization of alkenes, see for example US 2002/0142912; U.S. Pat. Nos. 6,900,321; and 6,103,657, where the ligands have been used in complexes in which the ligands are coordinated in a bidentate fashion to the transition metal atom.
WO 2005/095469 shows catalyst compounds that use tridentate ligands through two nitrogen atoms (one amido and one pyridyl) and one oxygen atom.
US 2004/0220050A1 and WO 2007/067965 disclose complexes in which the ligand is coordinated in a tridentate fashion through two nitrogen (one amido and one pyridyl) and one carbon (aryl anion) donor.
A key step in the activation of these complexes is the insertion of an alkene into the metal-aryl bond of the catalyst precursor (Froese, R. D. J. et al., J. Am. Chem. Soc. 2007, 129, pp. 7831-7840) to form an active catalyst that has both a five-membered and a seven-membered chelate ring.
WO 2010/037059 discloses pyridine containing amines for use in pharmaceutical applications.
U.S. Pat. No. 8,158,733 describes catalyst compositions featuring 2-(2-aryloxy)-8-anilinoquinoline, 2,8-bis(2-aryloxy)quinoline, and 2,8-bis(2-aryloxy)dihydroquinoline ligands that do not feature a tridentate NNN donor ligand.
US 2012/0016092 describes catalyst compositions containing 2-imino-8-anilinoquinoline and 2-aminoalkyl-8-anilinoquinoline ligands having a one-atom linker between the quinoline and the nitrogen donor at the 2-position of the quinoline ring.
US 2010/0227990 A1 discloses ligands that bind to the metal center with a NNC donor set instead of an NNN or NNP donor set.
WO 2002/38628 A2 discloses ligands that bind to the metal center with a NNC donor set instead of an NNN or NNP donor set.
WO 2016/102690 discloses a process for preparation of a branched polyolefin using a metal hydrocarbyl transfer agent.
Organometallics, 2012, 31, p. 3241 by Hu et al. describes catalyst compositions containing 2-aminoalkyl-8-quinolinolato ligands that do not feature a tridentate NNN donor ligand.
Organometallics, 2013, 32, p. 2685 by Nifant'ev et al. describes catalyst compositions containing 2,8-bis(2-aryloxy)dihydroquinoline ligands that do not feature a tridentate NNN donor ligand.
Dalton Transactions, 2013, 42, p. 1501 by Nifant'ev et al. describes catalyst compositions containing 2-aryl-8-arylaminoquinoline ligands that do not feature a tridentate NNN donor ligand.
U.S. Pat. No. 7,858,718 describes catalyst compositions containing 2-aryl-8-anilinoquinoline ligands that do not feature a tridentate NNN donor ligand.
U.S. Pat. No. 7,973,116 describes catalyst compositions containing pyridyldiamide ligands, e.g., a pyridine-based ligand not a quinoline-based ligand.
US 2014/0256893 discloses the use of chain transfer agents, such as diethyl zinc, with transition metal pyridyldiamide catalysts in polymerization processes.
Guerin, F.; McConville, D. H.; Vittal, J. J., Organometallics, 1996, 15, p. 5586, discloses a ligand family and group 4 complexes that use a NNN-donor set, but do not feature seven-membered chelate ring or either of dihydroindenyl- and tetrahydronaphthalenyl-groups.
Macromolecules, 2002, 35, 6760-6762 discloses propene polymerization with tetrakis(pentafluorophenyl)borate, 7-octenyldiisobutylaluminum, and racMe2Si(2-Me-indenyl)2ZrCl2 or Ph2C(cyclopentadienyl)(fluorenyl)ZrCl2 to produce polypropylene with octenyldiisobutylaluminum incorporated as a comonomer.
U.S. Pat. Nos. 7,973,116; 8,394,902; US 2011-0224391; US 2011-0301310 A1; and U.S. Ser. No. 61/815,065, filed Apr. 23, 2013, disclose pyridylamido transition metal complexes that do not feature dihydroindenyl- or tetrahydronaphthalenyl-groups.
References of interest also include: 1) Vaughan, A; Davis, D. S.; Hagadorn, J. R. in Comprehensive Polymer Science, Vol. 3, Chapter 20, “Industrial catalysts for alkene polymerization”; 2) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283; 3) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem. Int. Ed. 1999, 38, 428; 4) US 2011/021727; and 5) Zhang, et al., Tetrahedron, Vol. 69, No. 49, Dec. 1, 2013, pages 10644-10652.
There is still a need in the art for new and improved catalyst systems for the polymerization of olefins, in order to achieve specific polymer properties, such as long chain branching, high melting point, high molecular weights, to increase conversion or comonomer incorporation, or to alter comonomer distribution without deteriorating the resulting polymer's properties.